Reaktion #1005954

Reaktionsgleichung

2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoro-methyl)-1,3-thiazole-5-carboxylic acid

Thionyl chloride

→

title compound

Ausbeute 65.0%

{2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazol-5-yl}methanol

Ausbeute 65.0%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas then refluxed
2. 2
   Temperaturunder heating for 5 hours
3. 3
   SonstigeAfter removing the solvent
4. 4
   Sonstigeby evaporation
5. 5
   workup.DISSOLUTIONthe residues were dissolved in 1,4-dioxane (20 mL)
6. 6
   workup.ADDITIONadded dropwise to the mixture solution comprising water (30 mL), 1,4-dioxane (30 mL), and sodium borohydride (0.5 g) under ice cooling
7. 7
   workup.ADDITIONAfter the dropwise addition
8. 8
   Temperaturthe reaction solution was refluxed
9. 9
   Temperaturunder heating for one hour
10. 10
    TemperaturAfter cooling
11. 11
    workup.ADDITIONthe reaction solution was poured over ice water
12. 12
    Extraktionextracted with ethyl acetate
13. 13
    TemperaturAfter cooling
14. 14
    Extraktionthe extraction
15. 15
    workup.ADDITIONby adding water and ethyl acetate
16. 16
    TrocknenThe organic layer was dried over magnesium sulfate
17. 17
    SonstigeThe solvent was evaporated off under reduced pressure
18. 18
    Sonstigethe residue was then purified by a silica gel chromatography

Vorschrift

2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoro-methyl)-1,3-thiazole-5-carboxylic acid (2.2 g) was added to 1,2-dichloroethane (50 mL). Thionyl chloride (1.0 g) and one drop of N,N-dimethylformamide were added to the mixture, which was then refluxed under heating for 5 hours. After removing the solvent by evaporation, the residues were dissolved in 1,4-dioxane (20 mL), and then added dropwise to the mixture solution comprising water (30 mL), 1,4-dioxane (30 mL), and sodium borohydride (0.5 g) under ice cooling. After the dropwise addition was completed, the reaction solution was refluxed under heating for one hour. After cooling, the reaction solution was poured over ice water, and then extracted with ethyl acetate. After cooling, the extraction was again carried out by adding water and ethyl acetate. The organic layer was dried over magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was then purified by a silica gel chromatography to obtain the title compound (1.1 g, 65%).

Quelle